ON A JANUARY DAY IN 1904, two men sat idling in bulky, big-wheeled racecars on a stretch of wide, hard sand on the beach be­tween Day­tona and Ormond, Fla., ready for a one-mile, straight-ahead match race. The show­down was part of the Florida Speed Carnival—a few days of socializing and car racing along the beach featuring, mostly, well-to-do gentlemen-sportsmen. Though the automobile industry was little more than a decade old, numerous manufacturers in Europe and the United States were scrambling to establish their reputation, partly by building bigger engines and faster cars.

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The two drivers could not have been more different. William K. Vanderbilt II, known as Willie K. to his friends, was the great-grandson of Cornelius Vanderbilt and heir to a huge transportation fortune. His racer was a custom-built 90-hp Mercedes he'd imported from Germany and dubbed the "Ormond Flier." Vanderbilt had already set a one-mile speed record in the Flier, covering the distance in 39 seconds—92 mph. Vanderbilt's opponent was a mercenary—a daring professional driver named Barney Oldfield. A tenacious Toledo, Ohio, native, Oldfield had migrated from bicycle to car racing, worked briefly for Henry Ford, and set speed records that had transformed the former newsboy into a celebrity. Alex­ander Winton, owner of Cleveland-based Winton Car­riage Car Com­pany, founded in 1897 and the first firm to sell an automobile in the United States, had hired him to win races. Oldfield was driving the Winton Bullet II, whose predecessor had set the one-mile speed record at Ormond-Daytona two years earlier.

Vanderbilt wore a fur coat and gripped the wheel in tailored gloves. Oldfield chomped on the end of a cheap cigar—a trick that helped to preserve his teeth during bone-jarring races. When the pair roared off, 5,000 spectators (fashionable high-society types and "a sprinkling of open-mouthed crackers," according to one reporter) strained to see through the morning mist blowing in from the sea. At the quarter-mile mark Vanderbilt and Old­field were even, then Oldfield found more speed and began to pull away. It was the only race Vanderbilt lost all week. In his thunderous Mercedes, he won the remaining nine races, including the prestigious 50-mile champion­ship cup. As Motor Age observed, "every time Mr. Van­derbilt went over the course he returned with victory and records dangling from his motor."

Flush from his triumph, the 26-year-old Vanderbilt returned to New York and announced his intention to organize a major race on Long Island, where he owned an estate. It would be the first true international automobile road race in the United States. Vanderbilt had raced extensively in Europe, in French and German cars, but now he became focused on promoting the U.S. car industry. His motivation, he later explained, was that "foreign cars seemed to be always five years ahead of the American cars. If something could be done to induce foreign manufacturers to race in this country, our manufacturers would benefit."

Vanderbilt provided the inducement. His plan was for a grueling 300-mile race, and he commissioned Tiffany & Co. to make a 30-pound sterling-silver trophy adorned with a frieze of himself driving the Ormond Flier to a world's record. The race, like the trophy, was called the Vanderbilt Cup. The inaugural Vanderbilt Cup, in October 1904, attracted more than 25,000 spectators, and in the years that followed, the event became a glamorous happening—a sporting spectacle with huge crowds. The race attracted the world's best drivers (George Heath, Vincenzo Lancia, Louis Chevrolet, Eddie Rickenbacker and Oldfield, among them) and the world's top manufacturing marques (Panhard et Levassor, Darracq, Renault, Mercedes, Fiat). Though it lasted little more than a decade, the Vanderbilt Cup was one of the biggest sporting events of the early 20th century—and long before the Indianapolis 500 and NASCAR, it exerted an outsize influence on car racing and on America's automobile industry. It spurred carmakers to improve their technology, sparked the idea of using race victories to market cars and pioneered road building: In 1908 Vanderbilt built a stretch of concrete road for his race that was the first thoroughfare specifically for automobiles—a prototype for future highways. It was a more than credible legacy for a man of leisure who was largely kept away from the Vanderbilt family railroad business.

William Kissam Vanderbilt II was born in New York City in 1878, the second child and first son of William K. Vanderbilt and Alva Erskine Smith, who divorced in 1895. His great-grandfather, Cornelius "Commodore" Van­derbilt, was the shipping and railroad tycoon who, when asked about the discomfort of his train cars, famously snarled, "The public be damned." Willie's sister, Consuelo, married Charles Spencer-Churchill, the English Duke of Marlborough. Van­­der­bilt was raised in various family mansions on Long Island and in Newport, R.I., and traveled frequently to Europe, usually aboard one of his father's yachts. He was educated by tutors and at a private school, and would spend a year at Harvard, but he had too many passions and too much money for indulging them to remain a student.

The race was plagued by crowd-control problems. Fans along the course were sometimes hit and killed. (Library of Congress)

When he was 10, Willie's family were guests of the French Count de Dion, who took Willie for a spin on his novel three-wheeled, steam-powered contraption. The scion was entranced. In 1897 Willie's stepfather, Oliver H.P. Belmont, imported a French touring car to Newport. Two years later, 21-year-old Willie bought his own machine—a De Dion-Bouton motorized tricycle. He tootled around in it before a more powerful steam-engine car struck his fancy. Roaring around Newport in that vehicle, he frightened and angered the locals. There were no speed laws in the late 19th century, so police officers cited him for operating a steam boiler without an engineer's license. Ever on the lookout for a better toy, Willie soon discarded the steamer and imported a succession of Mercedes and French Mors cars.

Willie's penchant for risk-taking often got him in trouble as a young adult. He flipped a car, racing backward down a hill in Newport, and was lucky to escape serious injury. After he took possession of a Daimler Mercedes that he nicknamed the "White Ghost," he had a series of accidents. He hit a fish delivery wagon in New York City and ran into a little girl in Rhode Island, injuring her arm. Feeling persecuted by authorities, he once quipped: "Arrest me every day if you want to…it is nothing to pay fines for such sport."

In 1899 Vanderbilt married Virginia Graham Fair, an heiress whose father had made a fortune mining the Comstock Lode. The couple spent a lot of time on a family estate on Long Island, where farms were prevalent and the roads were fairly flat and straight. There, Vanderbilt could zip around with fewer worries—or so he thought. Farmers and workers soon became outraged by his disregard for their safety.

Vanderbilt organized some five-mile car races at Aquidneck Park, near Newport, in 1901 and 1902, and dominated them in a custom-made Daimler he called the "Red Devil." But he found the half-mile horse track less than fulfilling—the curves demanded that he slow down—and he returned to Europe to race. In 1902 Vanderbilt competed in a time trial at Achères, France, and set the world's record for a gasoline car at just under 66 mph. The following year he lined up for the prestigious Paris to Madrid race but broke down shortly after the start. That might have been a lucky break: Three spectators and four racers were killed in a succession of crashes; among the victims was famed French auto manufacturer Marcel Renault.

When Vanderbilt got back to the United States, he helped to establish the American Auto­mobile Association (AAA). His Long Island Motor Club was one of the organization's nine founding clubs, and in 1902 it hosted a 100-mile endurance contest. Billed as an exhibition of both mechanical progress and civic responsibility, the rules required all contestants to respect a
15 mph speed limit.

The 1904 Vanderbilt Cup—10 laps around a 30-mile course on Long Island's public roads—would have no speed limits. Indeed, the purpose of the race would be to showcase the best and the speediest cars. "I wanted to bring foreign drivers and their cars over here in the hope that America would wake up," Vanderbilt later explained.

While sportsmen were excited about the race, Long Island's farmers had a far different reaction. They re­sented the haughty millionaire drivers, opposed open-road racing in their counties and were incensed when signs posted along the race route—a triangular course comprising Jericho Turnpike, Massapequa-Hicksville Road and the new Hempstead-Bethpage Turnpike—warned locals to stay off the roads and pen up their livestock on race day, Saturday, October 4. Saturday was market day. They filed an injunction against the race, arguing that it was unconstitutional to deny the use of the public roads to citizens to gratify the whims of "purely pleasure seekers, who sought to do a thing merely to gratify an aristocratic taste." Whatever the motivation, Vanderbilt got his way: A judge ruled that the race could go ahead.

According to Howard Kroplick in his 2008 book Vanderbilt Cup Races of Long Island, "The race's daybreak start attracted thousands of adventurous souls who streamed into Long Island from New York City continuously on Friday night and early Saturday." The swells were dressed to the nines—men in fur overcoats and bowlers, women in well-tailored gowns. "With hotels and roadhouses overflowing, they camped, gambled, drank, socialized and established a tradition of revelry that became a hallmark of the event."

The Vanderbilt name drew many leading car manufacturers and drivers. Among the 18 entrants were six cars from France, five from Germany, six from the United States and two from Italy. The French cars included three 90-hp Panhards and an 80-hp De Dietrich. The driver of the De Dietrich, Fernand Gabriel, had finished second in the 1903 road race in Ireland organized by New York Herald publisher Gordon Bennett and was the winner of the doomed Paris-Madrid race. The German cars were all Mercedes. The only American car that had anything close to the power of the European machines was the 75-hp Simplex, owned and driven by Frank Croker, son of Tammany Hall boss Richard Croker.

Each car carried two men—the driver and a so-called mechanician who made repairs, worked a hand pump to maintain oil pressure and acted as navigator. Because the public roads were narrow, the cars were started at two-minute intervals to spread them out, and there were checkpoints at which the drivers were made to stop for inspections. Tire companies, including Michelin and B.F. Goodrich, manned outposts on the route to assist with tire changes. A huge, two-sided scoreboard was built in 1905 to help grandstand fans keep track of driver positions on the course.

The first race was thrilling and dangerous. The cars were fast but not easy to control. Their suspensions were rigid, and tire and brake technology had not kept pace with engine development. There were frequent blowouts and other mechanical problems—only nine of the 18 cars were still running at the halfway mark of the race. The first serious turn of the course, by the Jericho General Store and Jericho Hotel, was sharp and narrow, and drivers had to navigate through the surging crowd. Despite warnings from flagmen, spectators stepped into the road to get a look at the daring drivers and their ma­chines. Newspaper writers dubbed it the Curve of Death. George Heath, driver of a French Panhard, had complained before the race of "exceedingly dangerous" roads, adding, "If there are not lives lost at some of those sharp turns I shall be agreeably surprised." He was prescient: George Arents Jr., heir to a tobacco fortune, lost a tire on Hempstead Turnpike, near Queens, and flipped. Arents' mechanician, Carl Mensel, was crushed by the car and died. Arents was knocked unconscious but survived.

Heath, a British citizen, won the first Vanderbilt Cup in his Panhard. He completed the 10 laps in just under seven hours, averaging 62 mph. He was followed within a minute by a French driver, Albert Clément Jr. The grandstand crowd swarmed the finish line, forcing organizers to stop the race. American Herb Lytle in his little Ohio-built Pope-Toledo, the most underpowered car at the start, surprised everyone by being in third when the race was called.

New York newspapers trumpeted the race on their front pages the next day, noting that the event had elevated racing in America to European standards. The New York World crowed: "The winner of to-day's race will be acclaimed the greatest chauffeur in the world; his car will be proclaimed the best car for speed in the world….No road race of such importance has ever been held on this side of the Atlantic. Nothing like the speed that will be maintained over the 300 miles of the course has ever been made in the United States over such a stretch of ground…never before in this country has there been a contest in which the danger was so widespread."

The next year, the course was modified to eliminate some of the life-threatening turns, and the competition got tougher. Fiat entered five cars—one driven by the affable Vincenzo Lancia and another by a Swiss-born driver named Louis Chevrolet. Both would go on to start their own car companies. Lancia, in a 120-hp car, dominated the race and had a more than 30-mile lead when he had a flat tire. Eager to get back on the course after the repair, he pulled out in front of American driver Walter Christie, who hit Lancia's car in the rear. The resulting delay for more fixes cost the popular Italian the race. Frenchman Victor Hemery, in a Darracq, won the 1905 Vanderbilt Cup, and plucky American Joe Tracy took third in a Locomobile built in Bridgeport, Conn.

In 1906 the Vanderbilt Cup was the talk of the sporting world—and New York. The race inspired a Broadway musical titled The Vanderbilt Cup: 17-year-old Elsie Janis was the star, and Barney Oldfield made an onstage appearance. The race itself that year was distinguished and plagued by its huge crowd—an estimated quarter of a million people. Police and new 6-foot-high protective fencing could not keep fans off the course. Three spectators were struck by cars. Driver Elliot Shepard, Vanderbilt's cousin, hit and killed a man. Frenchman Louis Wagner, in a Darracq, led from start to finish—the third straight victory by a French car. Just before Wagner crossed the finish line, in front of a cheering grandstand crowd that included race referee Vanderbilt, starter Fred Wagner waved a checkered flag. By most accounts it was the first time that symbol of racing triumph was used to end a race. Wagner called the race "certainly the most nerve-wrenching contest in motoring history."

Vanderbilt believed the solution to the crowd problem was to rebuild the roads to new and higher standards: make them wider, pave them with concrete and separate their grades from all other intersecting roadways. Envisioning a fast road built just for cars, Vanderbilt organized a company and began construction of the Long Island Motor Parkway. In many ways it was the forerunner of today's superhighways. The 1907 race was canceled while nine miles of the planned 44 were constructed, and Vanderbilt reconstituted the Vanderbilt Cup in 1908. That year about one-third of the race was run along the new ribbon of highway.

That wasn't the only breakthrough. An American won the race for the first time. Brash, 23-year-old George Robertson, driving a Locomobile, won the 1908 race averaging 64 mph. The race was close, and as Robertson approached the final lap, Henry Ford, a director in Vanderbilt's parkway corporation whose company had just introduced the Model T, watched from the grandstand and was heard to shout, "I'd give five hundred dollars to see that American car win!" Robertson's win was testament both to his skill and to the innovations the races had spurred, including detachable rims that made it much easier to change tires. After the victory, the Locomobile Company of America installed tiny replicas of the Vanderbilt Cup on the hoods of its cars. Other American companies recognized the publicity potential of building racers specifically to compete in the event. Pope-Toledo had been the first carmaker to do it, and Apperson, Locomobile, Buick, Christie, Haynes, Knox, Thomas and Marmon all followed suit.

Harry Grant, driving a six-cylinder ALCO made by the American Locomotive Company, won both the 1909 and 1910 races. Like Loco­mobile before it, ALCO used the victories to sell its cars, buying advertisements celebrating the Vanderbilt Cup wins as "an unequalled performance by an unequalled car." Other manufacturers, including Oldsmobile, Pope-Hartford and Abbott-Detroit, did likewise, touting sundry 1910 race achievements in advertisements.

By then, however, enthusiasm for the race was starting to wane. In fact, 1910 was the last year the Vanderbilt Cup was held on Long Island. Bitterly cold weather reduced the crowd in 1909, and critics said the injuries to drivers, mechanics and bystanders had turned the race into a blood sport. Barney Oldfield announced he was retiring because he no longer wanted to draw crowds primarily interested in seeing him crash. The New York World published a scathing cartoon of the grim reaper holding the Vanderbilt Cup. From 1911 to 1916, the race was moved to other cities—first to Savannah, then Milwaukee, Santa Monica, San Francisco, then back to Santa Monica for what would be the final Vanderbilt Cup race.

That was largely the end of Vanderbilt's association with car racing. He was appointed to the board of the New York Central Railroad in 1910 and was elected president of the railroad in 1918 but resigned after just one year. In 1920 his father died, leaving him his estate, and William K. Vanderbilt II retired to a life of yachting and travel. He became an amateur naturalist, collecting specimens and artifacts from all over the world. In 1927, following his divorce from Virginia, Vanderbilt married a former wife of an heir to the John Wanamaker department store fortune. He built a Spanish Revival mansion on Long Island, named Eagle's Nest, which is today the Vanderbilt Museum. The Long Island Motor Parkway became the 44-mile toll road it was envisioned to be, but it was never profitable and in 1938 was turned over to Queens, Nassau and Suffolk counties in lieu of payment of back taxes. Vanderbilt died in 1944, age 65.

In a 2010 biography of Vanderbilt, Steven H. Gittelman wrote that "in many ways Willie K. was a visionary but did not possess the same genius for business as [his great-grandfather], diluting the railroad domination wielded by the founder." Vanderbilt was a sportsman who didn't have the desire, or need, to turn his passion for automobiles into profitable businesses. Still, he made a lasting mark with his race. Interviewed by the New York Times in 1934, on the 30th anniversary of the first Vanderbilt Cup, he acknowledged that the race was never the same after it left Long Island, but by then, he noted, "it did seem that all that could be hoped for had been accomplished." American auto man­ufacturers got a dramatic firsthand look at the quality of Euro­pean cars, and raised their standards to catch up. "Vanderbilt challenged the home industry to respond," says Howard Kroplick, who maintains a website devoted to the race (VanderbiltCupRaces.com), "and it did."

Timothy Messer-Kruse is the author of the forthcoming book Tycoons and Outlaws: The Class War That Shaped Auto Racing (Pivot Press).

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